EA026500B1 - Соединение 2-(пиридин-2-ил)-1,7-диазаспиро[4.4]нонан-6-он в качестве модулятора потенциал-зависимых натриевых каналов - Google Patents
Соединение 2-(пиридин-2-ил)-1,7-диазаспиро[4.4]нонан-6-он в качестве модулятора потенциал-зависимых натриевых каналов Download PDFInfo
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- EA026500B1 EA026500B1 EA201491251A EA201491251A EA026500B1 EA 026500 B1 EA026500 B1 EA 026500B1 EA 201491251 A EA201491251 A EA 201491251A EA 201491251 A EA201491251 A EA 201491251A EA 026500 B1 EA026500 B1 EA 026500B1
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- C—CHEMISTRY; METALLURGY
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Cited By (1)
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| RU2650523C1 (ru) * | 2017-07-24 | 2018-04-16 | федеральное государственное автономное образовательное учреждение высшего образования "Казанский (Приволжский) федеральный университет" (ФГАОУ ВО КФУ) | Производное пиридоксина для лечения эпилепсии |
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| GB201122113D0 (en) | 2011-12-22 | 2012-02-01 | Convergence Pharmaceuticals | Novel compounds |
| GB201209015D0 (en) | 2012-05-22 | 2012-07-04 | Convergence Pharmaceuticals | Novel compounds |
| MX2020003821A (es) | 2017-10-10 | 2023-01-12 | Biogen Inc | Proceso de elaboración de espiroderivados. |
| BR112020009361A2 (pt) | 2017-11-17 | 2020-10-13 | Cellix Bio Private Limited | composto de fórmula i, composição farmacêutica para tratar um distúrbio ocular ou complicações do mesmo, método de síntese de composto, método de tratamento de um distúrbio ocular ou complicações do mesmo em um indivíduo que precisa do mesmo e uso de um composto |
| CN113563258A (zh) * | 2021-07-29 | 2021-10-29 | 派普医药(江苏)有限公司 | 一种4-溴-2-(二氟甲基)-5-甲基吡啶的制备方法 |
| WO2023044364A1 (en) | 2021-09-15 | 2023-03-23 | Enko Chem, Inc. | Protoporphyrinogen oxidase inhibitors |
| AU2022349463A1 (en) * | 2021-09-24 | 2024-03-14 | Xenon Pharmaceuticals Inc. | Pyridinyl derivatives as sodium channel activators |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
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| WO2008090115A1 (en) * | 2007-01-24 | 2008-07-31 | Glaxo Group Limited | Pharmaceutical compositions comprising nk1 receptor antagonists and sodium channel blockers |
Family Cites Families (28)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5474995A (en) | 1993-06-24 | 1995-12-12 | Merck Frosst Canada, Inc. | Phenyl heterocycles as cox-2 inhibitors |
| US5466823A (en) | 1993-11-30 | 1995-11-14 | G.D. Searle & Co. | Substituted pyrazolyl benzenesulfonamides |
| JP3267300B2 (ja) | 1995-02-13 | 2002-03-18 | ジー．ディー．サール アンド カンパニー | 炎症の治療のための置換イソオキサゾール |
| US5633272A (en) | 1995-02-13 | 1997-05-27 | Talley; John J. | Substituted isoxazoles for the treatment of inflammation |
| UA57002C2 (uk) | 1995-10-13 | 2003-06-16 | Мерк Фросст Кенада Енд Ко./Мерк Фросст Кенада Енд Сі. | Похідне (метилсульфоніл)феніл-2-(5н)-фуранону, фармацевтична композиція та спосіб лікування |
| GEP20032998B (en) | 1996-04-12 | 2003-06-25 | Searle & Co | Substituted Benzenesulfonamide Derivatives as Prodrugs of Cox-2 Inhibitors |
| SI0912518T1 (en) | 1996-07-18 | 2003-12-31 | Merck Frosst Canada & Co. | Substituted pyridines as selective cyclooxygenase-2 inhibitors |
| CO4960662A1 (es) | 1997-08-28 | 2000-09-25 | Novartis Ag | Ciertos acidos 5-alquil-2-arilaminofenilaceticos y sus derivados |
| ATE281458T1 (de) | 1997-09-05 | 2004-11-15 | Glaxo Group Ltd | Pharmazeutische zusammensetzung, enthaltend 2,3- diaryl-pyrazolo(1,5-b)pyridazin derivate |
| ATE275148T1 (de) | 1998-11-03 | 2004-09-15 | Glaxo Group Ltd | Pyrazolopyridin derivative als selektive cox-2 inhibitoren |
| US6025683A (en) | 1998-12-23 | 2000-02-15 | Stryker Corporation | Motor control circuit for regulating a D.C. motor |
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| SE0302811D0 (sv) * | 2003-10-23 | 2003-10-23 | Astrazeneca Ab | Novel compounds |
| EP1943216B1 (en) | 2005-10-10 | 2010-06-30 | Glaxo Group Limited | Prolinamide derivatives as sodium channel modulators |
| US8143306B2 (en) | 2005-10-10 | 2012-03-27 | Convergence Pharmaceuticals Limited | Methods of treating bipolar disorders |
| GB0520578D0 (en) * | 2005-10-10 | 2005-11-16 | Glaxo Group Ltd | Novel compounds |
| TW200730494A (en) | 2005-10-10 | 2007-08-16 | Glaxo Group Ltd | Novel compounds |
| US7505330B2 (en) * | 2006-08-31 | 2009-03-17 | Micron Technology, Inc. | Phase-change random access memory employing read before write for resistance stabilization |
| GB0701365D0 (en) | 2007-01-24 | 2007-03-07 | Glaxo Group Ltd | Novel pharmaceutical compositions |
| US8093268B2 (en) | 2007-01-24 | 2012-01-10 | Glaxo Group Limited | Pharmaceutical compositions comprising 2-methoxy-5-(5-trifluoromethyl-tetrazol-1-yl-benzyl)-(2S-phenylpiperidin-3S-yl-) |
| GB0706630D0 (en) | 2007-04-04 | 2007-05-16 | Glaxo Group Ltd | Novel compounds |
| DK2477964T5 (en) | 2009-09-14 | 2015-05-26 | Convergence Pharmaceuticals | A process for the preparation of alpha-carboxamide |
| PE20170202A1 (es) * | 2009-10-14 | 2017-03-24 | Xenon Pharmaceuticals Inc | Metodos sinteticos para compuestos espiro-oxoindol |
| GB201122113D0 (en) | 2011-12-22 | 2012-02-01 | Convergence Pharmaceuticals | Novel compounds |
| GB201209015D0 (en) | 2012-05-22 | 2012-07-04 | Convergence Pharmaceuticals | Novel compounds |
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Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2007042240A1 (en) * | 2005-10-10 | 2007-04-19 | Glaxo Group Limited | Quaternary alpha-aminocarboxamide derivatives as modulators of voltage-gated sodium channels |
| WO2008090115A1 (en) * | 2007-01-24 | 2008-07-31 | Glaxo Group Limited | Pharmaceutical compositions comprising nk1 receptor antagonists and sodium channel blockers |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| RU2650523C1 (ru) * | 2017-07-24 | 2018-04-16 | федеральное государственное автономное образовательное учреждение высшего образования "Казанский (Приволжский) федеральный университет" (ФГАОУ ВО КФУ) | Производное пиридоксина для лечения эпилепсии |
| US10844018B2 (en) | 2017-07-24 | 2020-11-24 | Ao “Tatkhimfarmpreparaty” | Pyridoxine derivative for treatment of epilepsy |
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| CN104271581A (zh) | 2015-01-07 |
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| US20140350040A1 (en) | 2014-11-27 |
| KR20140113692A (ko) | 2014-09-24 |
| HK1203492A1 (en) | 2015-10-30 |
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| EA201491251A1 (ru) | 2014-11-28 |
| CA2858938A1 (en) | 2013-06-27 |
| JP2015502394A (ja) | 2015-01-22 |
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